Method for preparing nitrogen-containing aromatic compound by catalytic pyrolysis of organic material

Patent metadata

Field	Value
Publication number	US-9975859-B2
Application number	US-201615009499-A
Country	US
Kind code	B2
Filing date	Jan 28, 2016
Priority date	Aug 1, 2013
Publication date	May 22, 2018
Grant date	May 22, 2018

Abstract

Provided is a method for preparing a nitrogen-containing aromatic compound through catalytic pyrolysis from organic materials. The method comprises: feeding organic materials and a catalyst into a reactor, to enable the organic material to undergo reactions in the presence of nitrogen and under heating conditions, so as to generate a reaction system flow containing one or more nitrogen-containing aromatic compounds.

First claim

What is claimed is:

1. A method for preparing a nitrogen-containing aromatic compound by catalytic pyrolysis of an organic material, comprising:
feeding an organic material feed and a catalyst to a reactor; and
reacting the organic material feed under the catalysis of the catalyst in the presence of a carrier gas and under heating conditions in the reactor, to generate a reaction stream comprising one or more nitrogen-containing aromatic compounds, wherein the carrier gas comprises a mixture of NH 3 and inert gas in a molar ratio greater than 1:19;
wherein the nitrogen-containing aromatic compound comprises pyrazine compounds, pyridine compounds, pyrrole compounds, indole compounds, aniline compounds or a combination thereof;
wherein the reaction temperature in the reactor is 300° C. to 800° C., and as the temperature increases, the selectivity towards pyrrole compounds decreases and the selectivity towards indole compounds and aniline compounds increases.

2. The method of claim 1 , further comprising:
separating at least a part of the nitrogen-containing aromatic compounds in the reaction stream, to obtain a product stream comprising the separated nitrogen-containing aromatic compounds and a recycle stream; and
feeding at least a part of the recycle stream to the reactor.

3. The method of claim 1 , wherein the catalyst comprises one or more of a zeolite catalyst, a non-zeolite catalyst, a metal catalyst and/or a metal oxide catalyst.

4. The method of claim 1 , wherein the catalyst comprises γ-Al 2 O 3 , SiO 2 —Al 2 O 3 , WO 3 /ZrO 2 , SO 4 2− /ZrO 2 , MCM-41, ZK-5, ZSM-23, SSZ-20, β-zeolite, Y-zeolite, ZSM-5 and/or HZ SM-5.

5. The method of claim 1 , wherein the catalyst has a SiO 2 /Al 2 O 3 ratio of 15:1 to 200:1.

6. The method of claim 1 , wherein the mass ratio of the catalyst to the organic material is 1:100 to 100:1.

7. The method of claim 1 , wherein the catalyst comprises a plurality of pores.

8. The method of claim 7 , wherein at least about 95% of pores of one or more catalysts have smallest cross-sectional diameters that lie within a first size distribution and a second size distribution; at least 5% of pores have smallest cross-sectional diameters that lie within the first size distribution; at least about 5% of pores have smallest cross-sectional diameters that lie within the second size distribution; and the first size distribution and the second size distribution do not overlap.

9. The method of claim 1 , wherein the catalyst contains one or more of the following doping metals: Cu, Mn, Co, Fe, Ni, Zn, Ga, Pt, In, Ru, Rh, Ir, Pt, Pd, Au, Re, Tl and lanthanide metals.

10. The method of claim 9 , wherein the doping metal is doped into the catalyst by dry/wet impregnation or ion exchange.

11. The method of claim 1 , wherein the carrier gas further comprises an inert gas.

12. The method of claim 1 , wherein the organic material comprises a biomass material.

13. The method of claim 12 , wherein the organic material comprises agricultural and municipal solid waste, food waste, animal waste, carbohydrates, lignocellulose or a combination thereof.

14. The method of claim 12 , wherein the organic material comprises wood, bagasse, bamboo, corn straws, waste paper, rapeseed meal, Jatropha curcas meal, soybean meal, lee, waste proteins, microalgae or a combination thereof.

15. The method of claim 12 , wherein the organic material comprises glucose, cellobiose, cellulose, starch, xylose, xylitol, xylan, chitosan, chitin, sucrose, fructose, aqueous glucose solution, furan, methylfuran, 2,5-dimethylfuran, furfural, 5-hydroxymethylfurfural, 5-methylfurfural, γ-valerolactone, bio-oils, water-soluble bio-oils, water-insoluble bio-oils or a combination thereof.

16. The method of claim 1 , wherein the nitrogen-containing aromatic compound comprises pyrazine, 2-methylpyrazine, 2,5-dimethylpyrazine, 2,6-dimethylpyrazine, pyridine, 2-methylpyridine, 3-methylpyridine, 4-methylpyridine, dimethylpyridine, pyrrole, 2-methylpyrrole, 3-methylpyrrole, dimethylpyrrole, indole, methylindole, dimethylindole, aniline, o-methylaniline, m-methylaniline, p-methylaniline, dimethylaniline or a combination thereof.

17. The method of claim 1 , wherein the organic material is fed into the reactor with a weight hourly space velocity (WHSV) of 0.05 to 10.

18. The method of claim 11 , wherein the inert gas is nitrogen or helium.

19. The method of claim 13 , wherein the organic material comprises carbohydrates.

Assignees

• Univ Science & Technology China

Inventors

• Zhang Ying
• Xu Lujiang
• Yao Qian

Classifications

• C07D207/323

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms · CPC title

• C07D241/12 Primary

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C10B53/02

  of cellulose-containing material (production of pyroligneous acid C10C5/00) · CPC title

• C07D207/32

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title